5-hexyl-2,2':5',2''-terthiophene | 151271-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-hexyl-2,2':5',2''-terthiophene
• 英文别名: 5-hexyl-2,2':5',2"-terthiophene；2-hexyl-5-(5-thiophen-2-ylthiophen-2-yl)thiophene
• CAS: 151271-42-0
• 化学式: C₁₈H₂₀S₃
• 分子量: 332.555
• InChiKey: LBMUANVIIFUZKC-UHFFFAOYSA-N

物化性质

• 熔点：
  66 °C
• 沸点：
  428.5±40.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5-hexyl-2,2':5',2''-terthiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到5''-bromo-5-hexyl-[2,2';5',2'']terthiophene
  参考文献：
  名称：

  具有正己基端基的四面体寡聚噻吩的合成，电子和形态学性质

  摘要：

  一系列在末端噻吩环的α位带有正己基的四面体寡聚噻吩（（n- C 6 H 13（C 4 H 2 S）n）4 C（Hex-T n TM; n = 1– 4）是由Kosugi–Migita–Stille耦合合成的，是一个关键反应。由于末端正己基团提供了更高的溶解度，因此成功获得了最大的同系物（n = 4）。较小的导数（n = 1，2）是液态物质，而较大的导数（n＝ 3，4）为固体。Hex-T3 TM可能是由于堆积力而在晶体中的相邻噻吩环之间部分采用了顺式构象。Hex‐T3 TM不仅以结晶态出现，而且以非晶态出现，在高达80°C的温度下稳定。无论端基如何，与相应的线性类似物相比，n = 2的衍生物均显示具有大的斯托克斯位移的宽荧光，从而表明联噻吩部分之间存在分子内相互作用。通过循环伏安法测量，Hex-T3 TM的自由基阳离子中还建议了对噻吩支之间的相互作用。

  DOI：

  10.1002/asia.201100639
• 作为产物：
  描述：

  2,2'-联二噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四甲基乙二胺 、 溶剂黄146 、 zinc(II) chloride 、 Pd(PPh3)4 作用下， 以 氯仿 为溶剂， 生成 5-hexyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Molecular engineering of organic semiconductors: design of self-assembly properties in conjugated thiophene oligomers

  摘要：

  In order to analyze the correlation between charge transport and structural properties in conjugated oligomers, sexithiophene, 6T, was substituted by hexyl groups, both on the terminal alpha positions (alpha,omegaDH6T) and as pendant groups in the beta position (beta,beta'DH6T). Structural characterizations by X-ray diffraction show that vacuum-evaporated thin films of 6T and alpha,omegaDH6T consist of layered structures in a monoclinic arrangement, with all-trans planar molecules standing on the substrate. When compared to 6T, alpha,omegaDH6T is mainly characterized by a very large increase of molecular organization at the mesoscopic level, evidenced by a much longer range ordering. Electrical characterizations indicate that the conductivity of alpha,omegaDH6T is largely anisotropic, with a ratio of 120 in favor of the conductivity parallel to the substrate plane, i.e. along the stacking axis. The charge carrier mobility, determined on field-effect transistors fabricated from these conjugated oligomers, also shows an increase by a factor of 25 when passing from 6T to alpha,omegaDH6T, reaching a value of 5 x 10(-2) cm2 V-1 s-1. In contrast, beta,beta'DH6T presents very low conductivity and mobility, the latter being below detection limit. These results are attributed to the self-assembly properties brought by alkyl groups in the alpha,omega position.

  DOI：

  10.1021/ja00072a026

文献信息

• [EN] PERYLENE TETRACARBOXIMIDE DERIVATIVES FOR PHOTOVOLTAIC DEVICES<br/>[FR] DÉRIVÉS DE PÉRYLÈNE TÉTRACARBOXIMIDE POUR DES DISPOSITIFS PHOTOVOLTAÏQUES
  申请人：SOLVAY

  公开号：WO2010012710A1

  公开（公告）日：2010-02-04

  The compounds of the present invention are represented by the following formula (I): wherein M is represented by the following formula: with R1, R2, R3, R4, R5, R6, R7, R8, R10, R11, X1, X2, X3, L, a, b, c, d, e, x, y, and z defined herein.

  本发明的化合物由以下公式（I）表示：其中M由以下公式表示：其中R1、R2、R3、R4、R5、R6、R7、R8、R10、R11、X1、X2、X3、L、a、b、c、d、e、x、y和z在此定义。
• 基于螺[芴-9,9`-氧杂蒽]的有机小分子空穴传输材料及其制备方法和应用
  申请人：南昌航空大学

  公开号：CN112250677A

  公开（公告）日：2021-01-22

  本发明公开了一种基于螺[芴‑9,9'‑氧杂蒽]的有机小分子空穴传输材料及其制备方法和应用，该有机小分子空穴传输材料以螺[芴‑9,9'‑氧杂蒽]为核，具有良好的无定形态和优异的溶解性能；侧链加以不同个数的噻吩基团，通过其高电子密度、优异的载流子传输能力、可控的光学及电化学性质等特点，赋予材料更加优秀的物理及光电性能；末端烷基链的修饰增加其溶解性，有利于材料的成膜性，更易于加工；同时通过简单的合成路线合成，并且原料易得，成本低廉；该有机小分子空穴传输材料应用于全无机钙钛矿太阳能电池，其电池效率相较于原始的电池效率为更高，说明其对提高全无机钙钛矿太阳能电池效率具有实际意义。
• Symmetrical and Nonsymmetrical Liquid Crystalline Oligothiophenes: Convenient Synthesis and Transition-Temperature Engineering
  作者：Julie Leroy、Nicolas Boucher、Sergey Sergeyev、Michele Sferrazza、Yves Henri Geerts

  DOI：10.1002/ejoc.200600850

  日期：2007.3

  the aromatic core with two identical branched alkyl chains and (ii) desymmetrization of the molecule with two alkyl substituents of different length or structure. Key steps in the synthesis of symmetrical and nonsymmetrical terthiophenes and quaterthiophenes involve Suzuki coupling and carbanion alkylation. A well-adjusted balance between the π–π stacking of the aromatic core and the disorder caused

  描述了液晶低聚噻吩中转变温度工程的两种方法：(i) 在芳香核处用两个相同的支链烷基取代，以及 (ii) 用两个不同长度或结构的烷基取代基使分子去对称化。对称和非对称三联噻吩和四联噻吩合成的关键步骤涉及 Suzuki 偶联和碳负离子烷基化。芳香核的 π-π 堆积与外围烷基链引起的无序之间的良好平衡被证明对于控制低聚噻吩介晶的热致行为很重要。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Three-dimensional tetra(oligothienyl)silanes as donor material for organic solar cells
  作者：Sophie Roquet、R?mi de Bettignies、Philippe Leriche、Antonio Cravino、Jean Roncali

  DOI：10.1039/b604261a

  日期：——

  Tetrahedral conjugated systems involving four conjugated oligothiophene chains fixed onto a central silicon node (1, 2) have been synthesized and used as donor materials in hetero-junction solar cells. Bilayer solar cells have been realized by thermal evaporation of compounds 1 and 2 as donors and N,N′-bis-tridecylperylenedicarboxyimide as an acceptor. Comparison of the performances of these devices to those of a reference system based on dihexylterthienyl (H3T) shows that despite comparable effective conjugation lengths, the 3D compounds 1 and 2 lead to a power conversion efficiency four–five times higher, suggesting better absorption of the incident light and better hole transport properties. Whereas fabrication of bulk hetero-junction with H3T was prevented by the lack of film forming properties, a prototype bulk hetero-junction based on compound 2 as the donor and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as the acceptor has been realized. A short-circuit current density of 1.13 mA cm−2 and a power conversion efficiency of 0.30% has been measured under AM 1.5 simulated solar irradiation at 80 mW cm−2.

  四面体共轭体系包括固定在中央硅节点上的四条共轭低聚噻吩链（1、2），已被合成并用作异质结太阳能电池的供体材料。以化合物 1 和 2 作为给体，以 N,N′-双十三烷基过二羧酰亚胺作为受体，通过热蒸发实现了双层太阳能电池。将这些器件的性能与基于二己基三噻吩（H3T）的参考系统的性能进行比较后发现，尽管有效共轭长度相当，但三维化合物 1 和 2 的功率转换效率要高出四至五倍，这表明它们对入射光的吸收更好，空穴传输性能也更好。由于 H3T 缺乏成膜特性，因此无法制作体异质结，而以化合物 2 为供体、[6,6]-苯基-C61-丁酸甲酯（PCBM）为受体的体异质结原型已经实现。在 80 mW cm-2 的 AM 1.5 模拟太阳辐照条件下，测得短路电流密度为 1.13 mA cm-2，功率转换效率为 0.30%。
• Syntheses and Properties of Oligothiophenes with Cyano and Hexyl Groups
  作者：Hiroshi Wada、Tomohiro Taguchi、Masanao Goto、Takuya Kambayashi、Takehiko Mori、Ken Ishikawa、Hideo Takezoe

  DOI：10.1246/cl.2006.280

  日期：2006.3

  Syntheses of new oligothiophenes which have cyano and hexyl groups at the ends of quarter- and ter-thiophenes are described. The observations of DSC and polarizing microscopy indicate the presence of liquid-crystalline (LC) phases over a wide temperature range. The energy gaps are discussed on the basis of the absorption and photoluminescence (PL) spectra and cyclic voltammetry. Thin films of oligothiophenes fabricated by vacuum deposition are investigated by AFM and XRD measurements.

  介绍了在四分之一噻吩和三噻吩末端带有氰基和己基的新型低聚噻吩的合成过程。DSC 和偏振显微镜的观察结果表明，在很宽的温度范围内都存在液晶（LC）相。根据吸收和光致发光（PL）光谱以及循环伏安法讨论了能隙问题。通过原子力显微镜 (AFM) 和 X 射线衍射 (XRD) 测量研究了通过真空沉积制造的低聚噻吩薄膜。